Holiday rentals in Lakeland-Winter Haven Metropolitan Area

Historic Downtown Bungalow w/piano

NO PET OR CLEANING FEES. The Daugherty House, a refurbished, downtown Lakeland, 1918 historic, 3 bed, 2 bath bungalow, between Lake Mirror and Lake Morton, features a 1907 upright piano, beautiful bedrooms with new mattresses and box springs, a spacious rocking chair front porch, cozy Florida room with a fold out couch, a gas fireplace, and memorabilia from Lakeland's history. The home's filled with antiques and modern conveniences, and the kitchen has all your cooking needs. CLICK SHOW MORE.

Paradise and Palmetto

Nestled in the charming Lake Morton Historic District on Palmetto Street, this completely detached suite is just a 5-min walk from some of Lakeland’s best gems! Downtown is just minutes away. Within walking distance, you’ll also find the public library, art museum, Lake Morton, Black and Brew and several other dining options. For those visiting local schools, Florida Southern College is less than a mile away, and Southeastern University is under three miles, making for quick and easy access.

Downtown Lkld-Urban Luxury Loft

Discover urban comfort in our Downtown Lakeland Studio Loft! This trendy third floor apartment accommodates 4 guests, boasting open industrial ceilings and historic brick walls that add a chic touch to the space. The floor to ceiling windows bring in gorgeous natural sunlight. Step outside and immerse yourself in the heart of the city, with cafes, shops, and attractions just a stroll away. Whether you're here for business or leisure, our loft offers the perfect blend of style and convenience!

Glam Townhouse in Downtown Lakeland - 2bed/2bath

Location, Comfort, and Privacy! We have all you look for one night or extended stay. This apartment was newly remodeled and designed for you to feel like home. Private garage, lock code system (key-less). Walking distance from Lake Hollingsworth, Morton, local coffee shops, restaurants, gas stations, etc. Lakeland is also conveniently located between Orlando and Tampa. 40minutes from Disney & Bush Gardens, 30min to Legoland, 1 hour from Orlando/Universal, and the gorgeous beaches on the gulf.

The Woodsy Weekender

Take it easy at this unique and tranquil getaway in the woods. Wake up in one of our cozy queen or full sized beds, and enjoy coffee and hot chocolate on the 2nd story deck. 10 minutes from downtown Lakeland, spend your day walking our beautiful lakes and eating at our foodie hotspots. End your day back the at Woodsy Weekender making dinner in our full kitchen and sipping wine on the screened in back porch swings watching the sunset. The perfect little "Safe Haven" cabin for all occasions.

Matty’s Citrus Connection

You are going to love this Citrus themed hideaway with its Old Florida feel that takes you back to simpler times. Rest and relax in this backyard paradise while enjoying all that Lakeland has to offer. Whether you choose a relaxing day enjoying the many local activities , take a day trip to a beautiful Florida-beach , or decide to visit one of Florida’s theme parks , this is the place to stay . We are centrally located and have quick access to Polk Pkwy , so your adventures are unlimited .

Romantic Lakefront – Feed Swans – Walkable Dining

Discover SWAN LAKE VACATIONS. Swan elegance meets city charm steps away. Highlights: • Lake Views • Downtown Stroll • King-sized bed • Modern Comfort • Full Kitchen • Semiprivate Patio • Between Tampa & Orlando Why Swan Lake Vacations? • Central Hub • Safety Assurance • Easy drive to beaches and Walt Disney World • Experienced Hosts Escape to Swan Lake Vacations—a place where swans grace the surroundings next to quaint downtown life. Book for a perfect blend of nature and urban comfort!

Gorgeous Gem in the Heart of Lakeland

LOCATION, LOCATION! This gorgeous, spacious, newly renovated home is located on one of the most desired and safest streets in all of Lakeland, and steps away from the beautiful Lake Hollingsworth and Trail. Close to the lake, and a short drive to downtown Lakeland, this gem is in the perfect location! This home features zero gravity beds, a gourmet kitchen, private laundry, smart TVs and WiFi, comfortable sofas with ample seating for entertainment, dining and more. You'll love this place!

Charming Historic Area Retreat!

Welcome to our charming one-bedroom short-term rental nestled in the scenic Lake Morton Historic District and conveniently located near the prestigious Florida Southern College. This thoughtfully designed accommodation offers a perfect blend of modern comfort and historic charm. Situated just a stone's throw away from the beautiful Lake Hollingsworth and Lake Morton our property provides an easy access to leisurely strolls around the lake and jogging trails.

TRENDY TOWNHOME *Btw beach & Disney+ smart TVs*

The BEST home and BEST service in the state of Florida. Modern, trendy townhome right off highway I-4 between Disney and Gulf Beaches! 3 bed, 2.5 bath townhome. 3 smart Tv’s to make your vacation that much more relaxing. And newly renovated kitchen, stocked with every appliance for short or long term stays. You won't find a better place in lakeland whether you are hosting a couples getaway, traveling for work, or vacationing with your family!

Hidden Ruby Apartment

Your family will be close to everything when you stay at this centrally-located place. Within walking distance to restaurants, major grocery stores, parks, and much more. Midway between major cities of Orlando and Tampa for the urban seekers. Reserved guest parking, front porch sitting area, washer and dryer, work station, and a children-safe environment. This apartment was designed to accommodate all of your needs.

La Casita Azul

The Little Blue House is a studio,guest house in our backyard. Separate entrance on the opposite side of the main house. This cozy comfortable room has a microwave, small refrigerator/freezer, and Kurig coffee maker( coffee included).It is perfectly located in the historic East Lake Morton, walking distance to Lake Morton, Lake Mirror, and downtown Lakeland. Perfect location to enjoy Lakeland.